Hydrochloric Acid → HCID 11633706, compound

HRID 724717Notes

Reaction equation

HRID 724717 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]2)=[C:17]([CH3:29])[CH:16]=1)[C:10]([O:12]C)=[O:11].C(N(CC)CC)C.Cl[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39].[OH-].[Li+].Cl>CO.O>[CH2:41]([O:40][C:38]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]2)=[C:17]([CH3:29])[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:39])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 11568380HCID 11568380, compound

Product 1

HCID 11633706HCID 11633706, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Methyl (2S)-2-amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-methylphenyl]propanoate trifluoroacetate (286 mg, 0.649 mmol) in methanol (7.0 mL) was treated with triethylamine (362 μL, 2.60 mmol) and cooled to 0° C. Benzyl chloroformate (116 μL, 0.812 mmol) was added and the solution stirred for 2 h. 2 M lithium hydroxide in water (0.81 mL) was added and the solution stirred for an additional 1 h. The reaction soluiton was acidified with 1 N HCl and extracted with ethyl acetate. The crude product was used in the next step without purification. MF=C21H22N2O7S; LCMS found for C21H23N2O7S (M+H)+: m/z=447.

Workup

  1. stirringthe solution stirred for an additional 1 h
  2. extractionextracted with ethyl acetate
  3. customThe crude product was used in the next step without purification

Sources & evidence

ORD record
ord-623067992b684f55938c1c9892e5cb51
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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